Ask Isadora: All Dressed Up and No Place to Go

All Dressed Up and No Place To Go

* My wife and I are a 40 year old bisexual couple who have been married for 15 wonderful years. A few weeks ago my wife discovered a few photographs of a young woman in an old box I forgot I had. She asked me who this woman was and I said “It was me about twenty years ago.” We both laughed about it. I then told her I used to crossdress from the time I was 15 years old until my early twenties. My wife then decided to take me shopping for some skirts, high heels, etc. I dressed up and we had a great time dancing the night away. My question is since my wife and I feel too old and out of place to go to the local clubs are there any associations, get-together places or cross dressing clubs that we can go to in the Connecticut or Southern Mass. Area and not feel out of place to kick up our high heels?

It depends on how well you pass as a woman. There are places where dancing couples your age would not be in the least out of place and there are those night spots who would not welcome someone who looks like a man in a dress. There are chapters of The Society for the Second Self ( various places in the U.S. To find those where you and your wife would be welcome to socialize I’d try to connect with them or with or the Massachusettes based Free To Be She organization at for recommendations. By the way, you’re very lucky to have your wife enjoy your recreation. I hear from so many men who have to stay closeted because their wives would be horrified.

* A new friend was helping me clean out my garage. It was hot and heavy work so he took off his shirt. I couldn’t help noticing he has several scars on his body. They don’t look medical, but I guess they could be. I’m thinking that since he took off his shirt in front of me he can’t be all that self-conscious about them. I am curious, but if they come from some terrible trauma like war wounds or a beating or something I might be bringing back memories best left undisturbed. Maybe he doesn’t want to talk about it. Can I ask him or let it go?

Tough call. You’re right about his willingness to remove his shirt but it still may not be something he wants to talk about. You said he is a new friend. Perhaps the subject will come up on its own or a likely conversational moment may provide an opening. If you become lovers, if that’s the nature of where this friendship is going, caressing his body in loving afterglow would give you a way to ask. I’m afraid I can’t give you any more guidance than that.

* I have a bet riding on this. Is it possible for a man to suck himself off? Is it possible for a woman to lick her own clit?

Have you ever seen any of those young Chinese acrobats and contortionists? If any female could do that, they could. I bet people would even pay to see it as an Olympic event. As for men, it’s apparently not all that uncommon if he is limber enough and has a long penis. Several men on my Sexuality Forum web site ( posted that they did or that they could when they were younger. Years ago I saw a man do it in a video entitled The Man From Nantuckett (You have to know the limerick).